Benzyl Chloride → HCID 66627851, compound

HRID 1970721Notes

Reaction equation

HRID 1970721 reaction equation
[CH2:1]([C:12]1[NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]=1)[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH2:2]([C:3]1[N:4]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH2:1][C:12]1[N:13]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 7503Benzyl Chloride2×HCID 11430Potassium CarbonateHCID 2543202,2'-ethane-1,2-diylbis(1H-benzimidazole)

Product 1

HCID 66627851HCID 66627851, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 0.5 g 2,2′-ethane-1,2-diylbis(1H-benzimidazole), 0.7 g potassium carbonate, 30 ml N,N-dimethylformamide and the mixture was stirred under nitrogen. 0.6 g Benzyl chloride were added and the mixture was heated to 60 C for 16 hours. Another 0.5 g benzyl chloride were added and the reaction was heated to 70 C for another 20 hours and then cooled to 22 C. The reaction was quenched with 30 ml water and the product was filtered and washed with water. The product was re-slurried in 80 ml hot acetonitrile, cooled, filtered and dried resulting in 0.35 g of a white solid.

Workup

  1. temperaturethe mixture was heated to 60 C for 16 hours
  2. temperaturethe reaction was heated to 70 C for another 20 hours
  3. temperaturecooled to 22 C
  4. customThe reaction was quenched with 30 ml water
  5. filtrationthe product was filtered
  6. washwashed with water
  7. temperaturecooled
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-a2222bcaba0d4bdfad5f9fa53b34e802
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

Loading…